The Tamsen Show: Bobbi Brown – How to Start Over When It Feels Impossible
Host: Tamsen Fadal
Guest: Bobbi Brown
Date: September 24, 2025
Episode Overview
In this empowering episode, Tamsen Fadal engages in an honest, inspiring conversation with Bobbi Brown, legendary entrepreneur, makeup artist, and founder of Jones Road. They delve into Bobbi's journey of reinvention, the personal and professional struggles she faced after leaving her namesake brand, and the wisdom she's gained through decades at the forefront of the beauty industry. Bobbi opens up about starting over in midlife, dealing with grief and rejection, trusting your instincts, and the importance of authenticity and inclusivity—reminding listeners it's never too late to begin again.
Key Discussion Points & Insights
1. The Unexpected End & Jump to Reinvention
-
Bobbi recounts the abrupt ending of her career at Bobbi Brown Cosmetics ([01:13]):
“When I ended my relationship with the corporation, it happened really suddenly. I mean, it was them that pulled the plug. So you feel bad and, you know, you feel like a loser... And it was tough. And so I really took two days off.”
– Bobbi Brown, [01:13] -
Her approach to moving forward:
“And then I'm like, okay, this isn't working for me. I gotta go do something...People wanna know all the time, how do you do this? You just start, you start. Stop asking, just start doing it.”
– Bobbi Brown, [01:31]
2. The Non-Compete Clause and Reinventing Herself
-
Bobbi shares the impact of her 25-year non-compete ([00:27], [13:42]):
“My husband called and said, it's all done. The deal's done except they want you to sign a 25 year non compete...I'm gonna be in my 60s, I'm not going to work then. So no big deal, I'll sign it. Well, guess what, I left at 59 and a half and I still don't own my name.”
– Bobbi Brown, [00:27] -
On continuing despite still not owning her name:
"I'm still Bobby Brown though. That's who I am as the person."
– Bobbi Brown, [14:26]
3. Reinvention, Fear, and Taking the First Step
-
On starting over and why action is everything:
“People want to know all the time, how do you do this? You just start. Like, I'm sure you thought about that before you started this chapter of your life. How do I do this? How do I do this? Stop asking. Just start doing it.”
– Bobbi Brown, [02:57] -
Failure as feedback:
"If you do something and say, well, that didn't work, or, I didn't get any, you know, eyeballs on that, okay, well, do something different then. Right?"
– Bobbi Brown, [03:25]
4. Defining Herself Beyond Conventional Rules & Age
-
Age as mindset, not a limitation:
"I don't want it to define me because really in my head I am the same 30 something year old kid. But I'm gonna, in two years I'll be 70, which is incredibly ridiculous."
– Bobbi Brown, [04:09] -
On making up her own rules:
“I’m definitely making up the rules. Like I’m, you know, people say that I’m a rule breaker. I’m not really a rule breaker. I just make up rules.”
– Bobbi Brown, [09:03]“Just to do what seems right, not what people think you should do, but just what makes sense...My biggest rule is just to be nice.”
– Bobbi Brown, [09:13]
5. The Importance of Authenticity & Inclusivity
-
Early career & entrepreneurial spirit:
“I found Emerson College and I went there and told them what I wanted to do…We have something called an interdisciplinary major. And I did. And that was really my start of being an entrepreneur.”
– Bobbi Brown, [06:34] -
Championing inclusivity in beauty:
"A company with my name on it...I didn't care what your skin color was. There was a color for you...I said, I'm not getting rid of the dark colors. If you're not selling enough of them, go get more customers, you know...But I never discontinued any of those colors."
– Bobbi Brown, [12:33]
6. Navigating Grief, Wellness & Healing
-
Coping with professional loss:
“There was the emotions of sadness, loss, anger, excitement...And fear. I mean, it was a very emotional time, but I needed something to do, so I started doing a bunch of projects…”
– Bobbi Brown, [16:03] -
On seeking emotional healing:
"I have this incredible husband that he just listened...But I ended up going to see my chiropractor. Now my chiropractor is this incredible guy who does emotional release techniques. It was really helpful...There was tapping. There was releasing...But it really works. I still see Dr. Jeff every week."
– Bobbi Brown, [23:35] -
Clarity through coaching & self-reflection:
“A dear friend...was my yoga instructor...said, I'm a life coach now...He made me take pictures of every eyesore [in my house]...And then he helped me see those things with love or make simple changes. And little by little, some of my things went away...It gave me clarity.”
– Bobbi Brown, [24:21]
7. Authentic Creation of Jones Road Beauty & Miracle Balm
-
The organic, messy process of starting Jones Road:
“I was building a kit...and I didn't want to use Bobbi Brown. I never used it since the day I left the company...I just didn't find things that I loved. I just thought there was something wrong with everything. And I just said, you know what? I wonder what's out there. And I found a chemist...I stuck my hand in it. It wasn't what I wanted, but I stuck my hand in it anyways. And I went like this, and I said, oh, my God, look at my face. I said, this is a miracle. And that's how Miracle Balm was born.”
– Bobbi Brown, [27:29] -
Evolution from her first company to now:
“In the very beginning...I was selling lipsticks out of my house. I was a new mom...So I had about a year of that...my husband would mail the things to people.”
– Bobbi Brown, [28:41]
8. Beauty, Self-Esteem, and Social Media
-
Why no-makeup makeup became her calling card:
"I really tried to conform to the makeup that was happening in the 80s, and I just thought it looked terrible...I just couldn't...And I started doing makeup my way, and it ended up on a cover of an Italian magazine. And then people were like, wow, this is nice."
– Bobbi Brown, [29:34] -
Natural makeup as self-esteem booster:
"I like enhancing and brightening and luminizing. I don't like trying to change the shape of something...I also think it's really bad for girls' self-esteem."
– Bobbi Brown, [32:54] -
On the pressures of social media and the importance of representation:
"There's a lot of things on social media that...make you feel bad, you know, from taller people, skinnier people, prettier people...But, you know...the important thing is to not make [girls] feel bad about who they are."
– Bobbi Brown, [33:40]
9. Memoir – Still Bobbi: Sharing Wisdom and a Blueprint for Reinvention
-
On writing her memoir and why now:
“I never thought about writing a memoir, really...She said...I want to do a memoir. I said, I don't want to write a memoir. I mean, I'm not that interesting...But she basically got me a really good book deal. So I said, all right, I'll write my story, right?”
– Bobbi Brown, [35:38] -
The book as lessons for all ages:
“I think younger girls...will see it as a blueprint for their life...And I think, you know, a lot of women that are trying to figure out reinvention...this book really was what she needed at this time...I know it doesn't matter. I'll figure it out.”
– Bobbi Brown, [36:37] -
Message to her younger self—and all women:
“I wanted to go back in time and tell those younger bobbies and all the girls to stay true to themselves and their vision and their belief in real beauty and to know that things will work out. Trust me, they really will.”
– Bobbi Brown, [37:42]
Notable Quotes & Moments
-
On resilience:
"I took two days off. And then I'm like, okay, this isn't working for me."
– Bobbi Brown, [22:06] -
On action versus deliberation:
"Stop asking. Just start doing it."
– Bobbi Brown, [02:57] -
Aging as a narrative:
"I don't want it [age] to define me...in my head I am the same 30 something year old kid."
– Bobbi Brown, [04:09] -
On inclusivity:
"If you're not selling enough [shades], go get more customers, you know...I never discontinued any of those colors."
– Bobbi Brown, [12:33] -
On legacy and identity:
"I'm still Bobby Brown though. That's who I am as the person."
– Bobbi Brown, [14:26] -
Advice for all ages:
"Stay true to themselves and their vision and their belief in real beauty and to know that things will work out. Trust me, they really will.”
– Bobbi Brown, [37:42]
Timestamps for Key Segments
- Non-compete and legacy: [00:27], [13:42]
- Just start—overcoming fear: [01:50], [02:57]
- Parenting, education, and making your own path: [05:38]–[07:08]
- Inclusivity in beauty industry: [12:33]–[13:19]
- Rejection, grief, and healing techniques: [21:29]–[24:19]
- Creating Jones Road & Miracle Balm: [27:29]–[29:04]
- Natural beauty philosophy & self-esteem: [29:34]–[32:54]
- Memoir and advice for reinvention: [35:38]–[37:42]
Tone & Style
Open, candid, and warmly encouraging—Bobbi Brown’s directness is matched by her humility and humor. She dispels glamorized myths of entrepreneurial success with real talk about setbacks and emotions while relentlessly advocating for authenticity, inclusivity, and kindness. Tamsen Fadal steers the conversation with empathy and relatability, extracting actionable lessons for every listener. Their exchange is genuine, uplifting, and loaded with practical wisdom.
For Listeners
Whether you’re contemplating a career shift, navigating menopause, or just in need of a boost to start something new, Bobbi Brown’s story in this episode is a testament to the power of resilience, self-trust, and reinvention at any age. Her journey is both a blueprint and an invitation: it's never too late to begin again.